Di Ciano first ran for Ward 5 in the 2010 election, losing narrowly to incumbent councillor Peter Milczyn.[1]
Again, running in Ward 5 for the 2014 Toronto municipal election, Di Ciano won the popular vote, beating out runner-up Kinga Surma who later ran and won as an MPP in the 2018 Ontario general election.
On March 8, 2018, the Toronto Star first reported that Di Ciano was being investigated by the OPP's anti-racket's branch, known for investigating enterprise crime and complex fraud, for "potential violations of the Municipal Elections Act."[2] On November 16, 2018, the OPP charged Di Ciano along with Mark Grimes for allegedly filing false campaign expenses for the 2014 municipal elections, contrary to the Municipal Elections Act.[3][4] On February 24, 2020, the charge was withdrawn by the Crown prosecutor. Assistant Crown attorney Michael Wilson told the media in possession of evidence to suggest that, during the 2014 Toronto municipal election, the campaign of Justin Di Ciano received the benefit of polling data from a company called Campaign Research that was not claimed on his financial statement-auditor's report" but “the Crown is not in a position to prove beyond a reasonable doubt that Justin Di Ciano personally requested or received this data or that he deliberately failed to report the receipt of that data when filing”.[5][6]
As a result of the ward boundary changes imposed on the City of Toronto by the Ontario Provincial Government in 2018 Ward 5 and Ward 6 were consolidated to make a new larger Ward 3. DiCiano announced he would not seek re-election in the larger new Ward during the 2018 Toronto municipal election.[7]